Potassium Carbonate → 3-[3-[4-(2-pyridinyl)-1-piperazinyl]propyl]-5-nitro-1H-indole

HRID 53148

반응식

HRID 53148 반응식
Br[CH2:2][CH2:3][CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=2)[NH:7][CH:6]=1.[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[N:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[N:23]1[CH2:24][CH2:25][N:26]([CH2:2][CH2:3][CH2:4][C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=3)[NH:7][CH:6]=2)[CH2:27][CH2:28]1

참가 물질

5

반응물 3

HCID 11430Potassium CarbonateHCID 944591-(2-Pyridyl)piperazineHCID 199620433-(3-Bromopropyl)-5-nitro-1H-indole

생성물 1

HCID 199620423-[3-[4-(2-pyridinyl)-1-piperazinyl]propyl]-5-nitro-1H-indole수율 39.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A mixture of 3-[3-bromopropyl]-5-nitro-1H-indole (1.4 g, 4.2 mmol), 1-(2-pyridinyl)-piperazine, (0.98 g, 5.09 mmol) and K2CO3 (1.4 g, 10.2 mmol) in 30 mL of acetonitrile was heated to reflux for 4 h. The reaction mixture was cooled, the solvent was removed and the residue dissolved in ethyl acetate and water. The aqueous layer was separated and extracted with ethyl acetate. The organic extracts were dried (MgSO4) and concentrated, and the gummy residue purified by flash silica gel chromatography (5% methanol in dichloromethane) to give 3-[3-[4-(2-pyridinyl)-1-piperazinyl]propyl]-5-nitro-1H-indole, (0.6 g, 36%) as a yellow solid: IR(KBr) 3182, 1520, 1330 cm-1 ; 1H NMR (DMSO-d6, 300 MHz) δ8.52 (d, J=2.24 Hz, 1H), 8.80 (dd, J=1.8, 4.8 Hz, 1H), 7.95 (dd, J=2.25, 9.0 Hz, 1H), 7.52-7.49 (m, 2H), 7.41 (s, 1H), 6.79 (d, J=8.6 Hz, 1H), 6.60 (t, J=6.6 Hz, 1H), 3.46 (t, J=4.7 Hz, 4H), 2.78 (t, J=7.4 Hz, 2H), 2.42 (t, J=5.0 Hz, 4H), 2.34 (t, J=6.9 HZ, 4H), 1.82 (dt, J=7.4, 6.9 Hz, 2H); MS (m/e) 365 (M+). Anal. Calcd for C20H23N5O2 : C, 65.73, H, 6.34, N 19.16; found C, 65.35, H, 6.26, N, 18.87.

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 4 h
  3. temperatureThe reaction mixture was cooled
  4. customthe solvent was removed
  5. dissolutionthe residue dissolved in ethyl acetate
  6. customThe aqueous layer was separated
  7. extractionextracted with ethyl acetate
  8. dry with materialThe organic extracts were dried (MgSO4)
  9. concentrationconcentrated
  10. customthe gummy residue purified by flash silica gel chromatography (5% methanol in dichloromethane)

출처 및 근거

ORD 기록
ord-5f20494e87c8408a88e8f1c8fd4a3e6c
출처 데이터셋
uspto-grants-1997_04
특허 번호
US05618816

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